The Perfect Weekend in New York City

Whether you prefer museum-hopping on the Upper East Side or bar-hopping in Brooklyn, there are plenty of ways to stay entertained in New York City, even when you're working with limited time. Here are a few tips for planning the perfect weekend in the Big Apple.

It may seem impossible to try and see the best of what New York City has to offer in three days, and we know what you’re thinking: Aren’t landmarks like the Empire State Building or Lincoln Center worth a visit? What about Lower Manhattan’s historical landmarks? And hey, where’s Queens? That’s all fair—but luckily, for all the changes that happen there every day, New York City isn’t going anywhere. Three days is just enough time to explore some of the neighborhood’s best attractions, whether it’s a hip new enclave, or an old-school neighborhood—you just have to know where to go and what to do.

Courtesy Neue Galerie

Travel back in time to 19th-century Vienna with a visit to the Neue Galerie.

Day 1: Uptown and Museum Mile

Few neighborhoods evoke the feeling of having traveled back to old-world New York City quite like the Upper East Side. While its eastern edge is more popular with families and twenty-somethings looking for budget apartments, the western side—bordered by Fifth Avenue and Central Park—is full of gorgeous mansions and neighborhood institutions (shops on Madison Avenue, museums on Fifth). You’d be remiss to skip a visit to the area, if for no other reason than everyone should visit the Metropolitan Museum of Art at least once in their lives.

STAY

The elegant Carlyle Hotel—an Art Deco landmark whose list of former guests includes the Kennedys, Truman Capote, and Princess Diana—is the perfect Uptown home base. Black-and-white marble floors and Goldenrod chaises fill the Dorothy Draper-designed lobby (the hotel was actually Draper’s first big decorating gig), while rooms are appointed with Louis XVI furnishings, Limoge china, and bedding by Yves Delorme—not to mention plush bath robes, slippers, and pillowcases monogrammed with guest’s initials.

PLAY

Several of Manhattan’s most impressive cultural institutions can be found along a 23-block stretch of Fifth Avenue known as Museum Mile. Start your culture crawl at the Metropolitan Museum of Art, which is packed with enough art and antiques (from Egyptian sarcophagi to Roman portrait busts) to keep even local New Yorkers amused for days. Afterwards, keep north: It’s nearly impossible to miss Frank Lloyd Wright’s modern masterpiece, the Guggenheim Museum. If you don’t have time to catch an exhibition, at the very least pop in to gawk at the lobby’s helix-like spiral staircase—or head to the Cooper Hewitt, which recently reopened after a years-long renovation.

EAT

Head back to the Neue Galerie, a turn-of-the-century Fifth Avenue mansion-turned-museum with an unparalleled collection of works by German and Austrian masters like Gustav Klimt (be sure to find his Portrait of Adele Bloch-Baueron the second floor), Egon Schiele, and Paul Klee. Stop in for a leisurely lunch at Cafe Sabarsky, the museum’s old-world Viennese kaffeehaus, where you can sink into Otto Wagner-upholstered banquettes for spaetzle, roasted bratwurst with Reisling sauerkraut, and Sachertorte.

PLAY

Cross Fifth Avenue and wander through Central Park. Just off of 79th Street you’ll find Belvedere Castle, a stone structure designed by Calvert Vaux with views of the entire park from its observation deck. Stroll south along the Mall, a leafy promenade lined with elm trees, and then Literary Walk, where you’ll find statues of writers like Robert Burns and William Shakespeare.

SHOP

At 66th Street, just west of Fifth Avenue, meander through the Children’s Zoo—you don’t have to be a kid to enjoy its trellised glass-roofed pergolas, whimsical bronze animal statues surrounding the Delacorte Music Clock tower, and 1908 merry-go-round with 57 carved horses and two decorative chariots. Exit the park at its southeastern corner and prepare for a little window shopping: the stretch of Fifth Avenue between 59th Street and 42nd Street is home to some of the city’s most storied—and high-end—shopping, from Holly Golightly’s Tiffany & Co. to Bergdorf Goodman and Henri Bendel.

EXPLORE

Next, head over to Grand Central Terminal—the Beaux Arts masterpiece is full of opulent flourishes, tiled arches, and ornate staircases. After you’ve gawked at the blue-and-gold celestial ceiling in the Main Concourse, head to the lower level to marvel at one of the station’s most secretive features: a whispering gallery, where you can speak softly and still be heard loud and clear by someone across the archway.

EAT

Just steps away, tucked beneath Ralphael Guastavino’s magnificent vaulted ceilings, is the legendary Grand Central Oyster Bar, a century-old landmark with 500 seats. Opt for one of the seafood platters, heaped high with oysters, shrimp, and other shellfish, or keep it simple with a bowl of New England or Manhattan-style clam chowder.

DRINK

End the evening with a drink at Bemelmans Bar at the Carlyle, named for Madeleinecreator Ludwig Bemelmans, whose whimsical murals cover the walls (back in the 1940s, he painted the murals in exchange for 18 months of lodging at the hotel). Settle into a leather banquette and sip one of the piano bar’s signature cocktails like the old-fashioned whiskey smash—it doesn’t get much more old New York than this.

Courtesy Russ & Daughters

Indulge in the most New York of snacks—smoke fish—at Russ & Daughters Cafe.

Day 2: Brooklyn

Yes, Brooklyn is all the rage these days, but the hype surrounding Kings County (which is actually NYC’s most populous borough) has reached a fever pitch, so much so that we’re in the backlash-to-the-Brooklyn-backlash mode. Don’t let that deter you from visiting: The chatter about Brooklyn’s shopping and dining scenes is justified, and there are unsung gems just waiting to be discovered in neighborhoods from Crown Heights to Williamsburg.

EAT

Instead of picking up an egg-and-cheese from a bodega, start your day with a proper breakfast sandwich from Mile End Deli. The Montreal-style eatery’s version includes house-cured bacon, fried eggs, and Quebec cheddar, all piled between two slices of rye bread.

SHOP

Head east to Crown Heights, where a new outpost of the Brooklyn Flea recently opened. During winter weekends, the ever-popular market moves indoors (in summer months, you’ll find the flea outdoors in Fort Greene and Williamsburg); trawl through stalls for vintage clothing, hand-made jewelry, antique furniture, retro treasures, and old-school collectibles. Fuel up with a cup of coffee from the Brooklyn Roasting Company, which has a kiosk in the market.

PLAY

Afterwards, you might need a break from the crowds and chaos of the city—and you’ll find it at the Brooklyn Botanic Garden, a 52-acre haven that flanks Prospect Park. It’s known for its more than 200 cherry trees (which bloom from early April to mid-May), but its sprawling lawns, winding paths, and tranquil gardens are worth the trip, no matter the season (don’t miss the Japanese Hill-and-Pond Garden, with a koi pond and cypress trees.)

EAT

Next up is Franny’s, one of Brooklyn’s new breed of pizzerias. Local ingredients are the stars of the wood-fired pies, which arrive with a blistered, perfectly crisp crust. The menu rotates seasonally, but year-round fare like the clam and chile pie is always a good bet.

PLAY

Hop a cab to Williamsburg, the once-industrial, now hipster-filled enclave. Here you’ll find excellent people watching—as well as one of the city’s quirkiest institutions, the City Reliquary Museum. It’s small (you can go through the whole thing in about an hour), but densely packed with New York City ephemera, including vintage Big Apple postcards, subway tokens, and even an old peep-show booth.

SHOP

Walk to Bedford Avenue, the neighborhood's main artery, where you’ll find stylish locals and great window-shopping at spots like Amarcord Vintage or Catbird. Off the main drag, there’s more shopping to be done: Beautiful Dreamers on Wythe Ave has an eclectic well-curated selection of clothing and accessories, while Bird offers beautiful womens- and menswear by indie designers.

DRINK

The roots of New York City’s expanding craft-beer scene can be found at the Brooklyn Brewery, a neighborhood staple since 1996. Tours of the brewery are offered on weekends, or you can try one of the beers on tap. (Brooklyn Lager is the classic choice, but we recommend the smooth brown ale or one of the seasonal brews.)

STAY

Located in a former textile factory, the Wythe Hotel is at the forefront of what may well become Brooklyn’s boutique hotel boom. The rooms are spacious and airy, with exposed brick and clean, industrial-inspired details. If you can, splurge on a Manhattan-facing room—the floor-to-ceiling windows have views of the Empire State and Chrysler buildings that will make your Instagram followers emerald with jealousy.

EAT AND DRINK

If you’re staying at the Wythe, have dinner at the hotel’s restaurant, Reynard. Opened by Andrew Tarlow, the man behind the neighborhood-defining restaurants Diner and Marlow & Sons, it regularly changes its menu to highlight what’s in season. (An all-day menu features bistro classics like an omelette and a burger.) After dinner, head up to the Ides Bar on the hotel’s sixth floor for a cocktail.

Day 3: East Village and the Lower East Side

Manhattan’s original bohemian enclave may look a bit different than it did a century ago—heck, even a few decades ago—but vestiges of the East Village and the Lower East Side’s past remain. Nowadays, these old-school institutions share space with neighborhood newcomers—shops, restaurants, and museums—that both honor the past while continuing to push the envelope, just like in the neighborhood’s good old days.

EAT

The century-old Russ & Daughters, one of NYC's classic cured-fish stores, recently opened a homey cafe just a few blocks from its original Lower East Side shop. The menu features the smoked fish that made the shop famous alongside other Jewish deli classics like matzoh ball soup, knishes, and potato latkes. The halvah ice cream, laced with salted caramel and topped with sesame seeds, is a must-try no matter the time of day.

PLAY

A few blocks south, travel back to the turn of the 20th century at the Tenement Museum. Located in a restored Orchard Street tenement, the institution leads tours that examine the history of both the neighborhood and the building itself (which was home to many immigrant families, and once had storefronts and a saloon on the ground floor).

SHOP

Head toward Chinatown, making sure to stop at some of the area’s best boutiques and long-standing establishments along the way: Lost Weekend NYC stocks surfer-cool wares (and also offers coffee, should you need to refuel); Moscot’s flagship has countless pairs of vintage eyeglasses frames; and the Museum at Eldridge Street, located in a converted synagogue, is one of the neighborhood’s oldest buildings.

EAT

For lunch, seek out tiny Doyers Street (GoogleMaps might help), a curved road that saw plenty of gang activity in the early 20th century—so much so that it was called "the Bloody Angle." The crime may be gone, but one relic of that era remains: Nom Wah Tea Parlor, a dim sum restaurant with a baby pink façade that opened in 1920. The parlor got a total facelift in 2010, but the menu’s hardly changed; sample traditional dishes like soup dumplings, pork buns, rice rolls, and even chicken feet.

EXPLORE

Head up the Bowery, keeping an eye out for the New Museum of Contemporary Art, the facade of which is often decorated with a site-specific piece of art (be it neon lettering or the hull of a two-mast ship). Then walk east on 2nd Street, passing the New York City Marble Cemetery, wedged in the middle of a city block, along the way. It’s open for tours intermittently.

SHOP

Take a detour into the St. Mark’s Bookshop, which recently relocated from its former location near Cooper Union to East 3rd Street. The decades-old indie haven is the definitive place to go if you’re looking for art books, independent publications (there’s an excellent selection of zines), or reads that explore the East Village’s revolutionary past.

EAT

For dinner, grab a seat at Prune, Gabrielle Hamilton’s snug, 30-seat boite at 1st and First Avenue, which has remained a well-loved local spot since it opened 15 years ago. Hamilton brings her idiosyncratic tastes to the menu, with surprisingly brilliant results; think sardines served with Triscuits crackers, or grilled pigeon served with toast. Desserts are similarly distinctive; one of the most popular is simply shaved dark chocolate served over bread.